High School Friends
author unknown
******
The following is a true story.
I won't say what age I was, but let's say it was around the junior
high/high school range. My friend John lived about half a mile down
the road from my house with his father, who was divorced. John's
sister had moved away to college a few months after my family had
moved into town from Seattle.
There was nothing unusual in the friendship, and neither of us had
ever thought much about anything other than what boys always think
about; girls. We'd hang out by the entrance to school and watch the
girls coming in, just knocked out by them. Neither of us were jocks,
or sports types, so we didn't have much chance to do anything about
it, of course. We were both thin for our age, and kept to ourselves
a lot. Neither of us had as much as touched a girl, though not for
any lack of trying or interest.
John's father worked clear across town, and often wouldn't get back
home until 8 or 9 in the evening. Sometimes I'd hang out at John's
until about then, watching TV, reading, horsing around. The house
had a basement, which was a combination rec room/storage room, not
much in it besides a few chairs, a couch, and a lot of boxes. When
John's sister had gone off to college, most of her stuff had been
stored down here so John's father could convert part of her room into
a workroom. Sometimes we went down to the basement to hang out, since
it was cooler there during the summer, and private.
One afternoon, we were hanging out down in the basement, and I started
poking around some of the boxes. I came across the boxes in which his
sister's stuff had been stored, and much to my delight, came out with
a bra. It wasn't fancy, or lace, just a plain white bra, but it was a
kick to know that she'd worn it. I dangled it in front of John, to
say look what I found. "Look familiar?" I said, and held it up against
my chest, my shirt on.
He laughed, and said to give it to him. I tossed it across, and he
did the same, holding the bra cups against his shirt and throwing
his chest out in an exaggerated way. It was funny, and we didn't
think too much about it. He asked me where I'd found it, and I showed
him. We dug through it, coming up with armfuls of her old clothes,
stuff she probably couldn't or didn't wear anymore, but which she
hadn't had time to give or throw away. By then it was getting late,
and I headed home.
The next day, I came over again, and the routine was pretty much the
same: TV, reading comics, hanging out. We ended up in the basement
again after a while, and I again started poking around in the box of
his sister's clothes. I pulled out the same bra again, and looked at
it more closely. It was about my size, and I mentioned it to John.
"Put it on," he said. "No way," I said. "What're you, chicken?" he
said. "It's not a big deal."
"If it's not a big deal, then you do it," I said. He shrugged and
got up, going to the box. He dug around until he came up with another
bra, a little nicer than the one I was holding: pink lace and pink
satin. He held it up and then slipped his arms through the straps,
holding it against his chest, over his shirt. He tried to reach
around back to close it, but couldn't, so he stood there with the
back trailing off. "See? No big deal."
I did the same, but it was tighter because I was a little bigger,
and I also had my shirt on. "Go ahead," John said, and I took off
my shirt, putting the bra on over my own skin. He did the same.
We couldn't figure out how to get it on _and_ close it, so first
he closed the one I was wearing, and I closed his. It felt...
funny. Tight, but I found I liked the tightness of it. It smelled
of his sister's perfume.
Which is as far as it got that day. We joked around a lot, looked
at each other and in the mirror, and after a while, I went home.
The next day, when I came over, it was as if a decision had already
been made, even though it had never been discussed. "Let's do it,"
John said. He rummaged through the boxes and pulled out the same bra,
now with a slip, plaid skirt, and blouse. "I don't know if this is
a good idea," I said. "It's okay," he said, "I tried it last night
after you left, before my dad got home. It's fun."
In a minute, he had pulled off his shirt and yanked off his jeans
and was pulling the clothes on, though he kept on his own shorts.
There was nothing sexy about it, he was just yanking them on. I
hesitated for a moment, then decided what the hell, and shucked
my own Levis and shirt, though also keeping my shorts on.
While he got into the clothes, I rummaged around in the box until
I came up with the plain bra, a pleated, checked skirt, a bright
green blouse, and a slip. It all went on fairly quickly, and we
turned to look at each other. It was almost funny; neither knew
much about dressing, neither of us had made any real attempt at
femininity, we were just wearing his sister's clothes, as prosaic
and straightforward as that.
We both admitted that it felt funny, but it also felt good, in a
strange kind of way. We really didn't know what else to do now
that we'd gotten this far, and lapsed back into our usual routine
of hanging out a little, and occasionally trying on something else
from one of the boxes. When we got down to the layer with the
lingerie and panties, we both hesitated. John picked up a pair of
light green panties. "You first," I said.
"Okay," he said, and turned away from me, yanking off his shorts
and stepping into the panties. I did the same, both of us turning
away even though we'd both seen each other naked in gym class. I
was hard by now, and he was the same, and we felt funny about
letting each other see that. Neither of us was terribly well
endowed; we couldn't have been more than five inches hard.
I pulled on a pair of plain white panties, which matched the bra
and slip. They felt snug and soft, and pulled me tight. I could
see John pushing down at his crotch to try and keep his erection
down, without much success. "You think this is what girls feel
like?" he asked. "I guess," I said.
"Feels good," he said, again pushing down at his erection, but the
more he tried to make it go away, the harder it got. I was in much
the same situation. After a minute, the temptation got to be too
much, and since he was already touching it, he started rubbing it
through the material. We didn't talk, didn't say anything at all
during this. I did the same. After just a couple of minutes, he
gasped, and came. I did the same, in my panties.
We were both embarrassed and excited. The first thing we did was
yank off the panties and dump them into the basement washing
machine, where John said he'd take care of them later. We didn't
get back into our regular clothes, though; only dug out fresh
pairs of panties from the boxes.
We talked about it for a minute, how good it felt, catching
occasional glimpses of each other in the mirror. Finally, he
said, "Wait," and dashed upstairs. He came back a minute later
with some of the magazines his father had bought and stashed in a
dresser drawer. We flipped through the pages, still dressed in his
sister's clothes, looking at the women and men fucking. It was a
strange situation to be dressed in a girl's clothes and looking at
the pictures from that perspective. As if it was us.
John was fascinated by one picture of a couple fucking doggy style.
The picture wasn't very good, and we couldn't figure out how they
were doing it. "Get down," he said. "What?" I said. "Look, you're
dressed like a girl, let's see. It's just pretend."
I hesitated, then finally agreed. By this time I was so excited that
my resistance was down. I got down on all fours on the basement floor,
my skirt hanging down around my knees. Holding the magazine, he got
behind me, between my knees, wearing his own skirt. He kept shifting
forward until his crotch bumped up against my butt. Even through two
pairs of skirts, slips and panties, I could feel his hardness. I
shifted forward a little. "Keep still," he said, and moved forward
again, pushing against me. He bumped back and forth a few times,
looking at the magazine, both of us still completely clothed.
"I can't feel anything," he said, disappointed. Then he reached down
and lifted my skirt up over my hips, the slip coming with it, and
leaned in again, grinding against me. With one set of skirt/slip out
of the way, I could feel the shape of him more clearly through his
own clothes and my panties. He put down the magazine and started
bumping against me rhythmically.
As if that weren't enough, between bumps he lifted the front of the
skirt and draped it over my back. Now we were just separated by the
two sets of panties. His cock was sticking hard straight out and
bumping straight into my butt through our panties. He must have
bumped it wrong at least once, because he shifted and now his panty
covered cock slipped into the crack of my ass, through my own panties,
and now rode up and down along the crack.
By now we were both breathing hard. I could feel his panties sliding
down off his cock with each push forward, until finally it was free
and sliding along my own panties, sometimes dipping below and slipping
between my legs. When it did, I brought my legs together to give him
something to shove into. The contact between my bare legs and his bare
cock seemed to excite him even further. "Good," is all he said.
After a while, he developed a rhythm, between my legs, then up along
my ass, then back again. He was gripping my hips to hold them still
while he stroked. My eyes were closed, savoring the sensation,
particularly when he slid between my legs, because then it was skin
on skin. Gradually I became aware that he was sliding the panties
slowly down my hips until they came off and dropped down to my knees.
His cock now rode along my bare ass, and I could hear him sigh with
pleasure. My ass was getting drenched with precum, making it easier
for his cock to slide along it.
On one stroke, he pulled back further than usual, and I felt his cock
bump against my asshole. I jumped slightly. "Hey," I said. "Sorry,"
he said, and went back to what he was doing...only to bump my asshole
again a minute later. "Cut it out," I said. "That's enough."
"It's okay," he said, pointing to the picture. "Look, they're doing
it that way." I said I didn't want to do that. "C'mon," he said, "if
you let me do you, I'll let you do me. Okay?"
I thought about it, his cock still sliding around between my legs and
along my ass, and it was so hot, so exciting, that finally I nodded
without saying anything. He backed up and again bumped his cock against
my asshole, which was already slick with his precum. He tried twice
to find the right angle, and bounced off. He grabbed me again through
the skirt, holding onto my hips as he again moved forward. His cock
found my asshole, and moved around a little, trying to find the right
angle. After a minute he found it, and he pushed slowly, easing in a
little. It hurt, but not too bad, and I closed my eyes, trying to
relax. He shoved a little more, and with a sudden pop he was inside
me. One more slow push and he was all the way in. The feeling was
intense, amazing. I tried to look back between my legs but the front
of my skirt hung down, cutting off the view.
He pulled back, and pushed in again, slowly at first, then faster.
I looked down to the magazine open beside me, of the woman being
fucked by a man behind her, and imagined myself to be her, dressed
in my skirt and blouse and bra. By now John was pounding hard
against me, fucking me fast and hard. The only sounds in the basement
were our gasps and the sound of our skin slapping. He shoved it in
harder and deeper into me with every thrust, holding onto my hips to
pull me back hard. Suddenly he got even harder inside me, and
straighter, and seemed to fill me even more as he cried out and I
felt something warm shoot out of him into the depths of my ass. He
shoved it all the way in and held it there as he spasmed, gasping
and shoving.
After a few moments, he pulled out with a wet sound and sat back
on his feet. "Wow," was all he could say. "You okay?" "Yeah," I
said, my ass sore but not too bad. He was still breathing hard.
Then it was my turn. He got on his hands and knees, ass facing me,
skirt raised and his panties down around his knees. I got behind
him and stroked myself until I had built up a good deal of pre-cum,
then positioned myself at his ass. I pushed forward. At first my
cock bent but didn't go in. Twice more it didn't go in, and I was
getting hot and frustrated when suddenly I found the right angle,
and with a sudden pop it slipped into his ass.
Inexperienced, eager to get going, I started stroking even before
I was halfway inside, though each thrust took me deeper inside
until I was completely buried in his ass. I grabbed his hips and
rode back and forth, sawing into his ass, my eyes half-closed so
that it looked as if I were assfucking a girl. And with his long
hair, and the skirt, it could easily have been a girl. With that
thought, I suddenly erupted in his ass, driving in hard as I came
deep inside him.
Being young, we did it twice more that afternoon when we finally
decided to quit, being sore and afraid of being caught as it got
later. After that, we met nearly every other day to dress and fuck
in his basement, always in his sister's clothes.
FIN